WO2016068633A2 - 함질소 다환 화합물 및 이를 이용한 유기발광소자 - Google Patents

함질소 다환 화합물 및 이를 이용한 유기발광소자 Download PDF

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WO2016068633A2
WO2016068633A2 PCT/KR2015/011526 KR2015011526W WO2016068633A2 WO 2016068633 A2 WO2016068633 A2 WO 2016068633A2 KR 2015011526 W KR2015011526 W KR 2015011526W WO 2016068633 A2 WO2016068633 A2 WO 2016068633A2
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compound
substituted
unsubstituted
preparation
formula
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PCT/KR2015/011526
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English (en)
French (fr)
Korean (ko)
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WO2016068633A3 (ko
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노영석
김기용
함효균
최진석
최대혁
음성진
이주동
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희성소재(주)
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Priority to CN201580058737.1A priority Critical patent/CN107001324B/zh
Priority to JP2017522865A priority patent/JP6615198B2/ja
Priority to EP15854965.9A priority patent/EP3214073B1/de
Priority to US15/523,155 priority patent/US10177319B2/en
Publication of WO2016068633A2 publication Critical patent/WO2016068633A2/ko
Publication of WO2016068633A3 publication Critical patent/WO2016068633A3/ko
Priority to US16/035,360 priority patent/US10672993B2/en

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Definitions

  • the present application relates to a novel nitrogen-containing polycyclic compound and an organic light emitting device comprising the same.
  • the electroluminescent device is a kind of self-luminous display device, and has an advantage of having a wide viewing angle, excellent contrast, and fast response speed.
  • the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light.
  • the organic thin film may be composed of a single layer or multiple layers as necessary.
  • the material of the organic thin film may have a light emitting function as necessary.
  • a compound which may itself constitute a light emitting layer may be used, or a compound which may serve as a host or a dopant of a host-dopant-based light emitting layer may be used.
  • a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.
  • the present application provides a novel nitrogen-containing polycyclic compound and an organic light emitting device comprising the same.
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; substituted or unsubstituted C 1 to C 60 alkyl; substituted or unsubstituted C 3 to C 60 cycloalkyl; substituted or Unsubstituted C 6 to C 60 aryl, and substituted or unsubstituted C 2 to C 60 heteroaryl,
  • a is an integer from 1 to 5
  • b is an integer of 0 to 6
  • c is an integer from 0 to 8
  • a, b and c are each 2 or more, a plurality of R 1 , R 2 and R 3 are the same or different from each other.
  • an organic light emitting device comprising an anode, a cathode and at least one organic material layer provided between the anode and the cathode, one or more layers of the organic material layer comprises a compound of the formula (1).
  • the compound described in this specification can be used as an organic material layer material of an organic light emitting element.
  • the compound may serve as a hole injection material, a hole transport material, a light emitting material, a hole blocking material, an electron transport material, an electron injection material in the organic light emitting device.
  • the compound of Formula 1 may be used as a material for electron injection and / or transport layer of the organic light emitting device.
  • the compound of Formula 1 may be used as a material of the hole blocking layer of the organic light emitting device.
  • the compound of Formula 1 may be used as a material of the light emitting layer of the organic light emitting device.
  • 1 to 3 illustrate the stacking order of electrodes and organic material layers of organic light emitting diodes according to exemplary embodiments of the present application.
  • FIG. 4 shows a PL measurement graph at 265 nm wavelength of Compound 37.
  • FIG. 6 shows a PL measurement graph at 298 nm wavelength of Compound 43.
  • FIG. 7 shows a LTPL measurement graph at 308 nm wavelength of Compound 43.
  • FIG. 8 shows a PL measurement graph at 278 nm wavelength of compound 44.
  • FIG. 9 shows a graph of LTPL measurements at 307 nm wavelength of compound 44.
  • FIG. 10 shows a PL measurement graph at 309 nm wavelength of Compound 76.
  • FIG. 11 shows a graph of LTPL measurements at 327 nm wavelength of compound 76.
  • FIG. 12 shows a PL measurement graph at 271 nm wavelength of Compound 98.
  • FIG. 13 shows a graph of LTPL measurements at 271 nm wavelength of compound 98.
  • FIG. 14 shows a PL measurement graph of 262 nm wavelength of Compound 248.
  • FIG. 15 shows a graph of LTPL measurements at 307 nm wavelength of compound 248.
  • FIG. 16 shows a PL measurement graph at 280 nm wavelength of Compound 267.
  • FIG. 17 shows a PL measurement graph of 325 nm wavelength of Compound 275.
  • Compounds described herein may be represented by the formula (1). Specifically, the compound of Formula 1 may be used as the organic material layer material of the organic light emitting device by the structural features of the core structure and substituents as described above.
  • Spirobifluorene skeleton of the formula (1) has a molecular form that is perpendicular to the conjugation (breaking) conjugation (conjugation) length can have a high value of the band gap and T1, the planarity is strong, the intermolecular distance when manufacturing the organic light emitting device It is short and can exhibit an excellent effect of electron transfer ability.
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group and can be interpreted as a substituent to which two phenyl groups are linked.
  • halogen includes F, Cl, Br and I.
  • alkyl includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents.
  • the carbon number of the alkyl may be 1 to 60, specifically 1 to 40, more specifically, 1 to 20, and may be 1 to 10.
  • alkenyl includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • the alkenyl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 2 to 20 carbon atoms, and 1 to 10 carbon atoms.
  • alkynyl includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • Alkynyl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 2 to 20 carbon atoms, and 2 to 10 carbon atoms.
  • cycloalkyl includes monocyclic or polycyclic having 3 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which cycloalkyl is directly connected or condensed with another ring group.
  • the other ring group may be cycloalkyl, but may also be other types of ring groups such as heterocycloalkyl, aryl, heteroaryl, and the like.
  • the cycloalkyl may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, more specifically 5 to 25 carbon atoms, 5 to 20 carbon atoms, and 5 to 10 carbon atoms.
  • the heterocycloalkyl includes O, S, Se, N or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which heterocycloalkyl is directly connected or condensed with another ring group.
  • the other ring group may be heterocycloalkyl, but may also be other types of ring groups such as cycloalkyl, aryl, heteroaryl, and the like.
  • the heterocycloalkyl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 3 to 25 carbon atoms, 3 to 20 carbon atoms, and 3 to 10 carbon atoms.
  • aryl includes monocyclic or polycyclic having 6 to 60 carbon atoms, and may be further substituted with other substituents.
  • polycyclic means a group in which aryl is directly connected or condensed with another ring group.
  • the other ring group may be aryl, but may also be other types of ring groups such as cycloalkyl, heterocycloalkyl, heteroaryl, and the like.
  • Aryl includes a spiro group.
  • the aryl may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, more specifically 6 to 25 carbon atoms, 6 to 20 carbon atoms, and 6 to 10 carbon atoms.
  • aryl examples include phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, chrysenyl, phenanthrenyl, perrylenyl, fluoranthenyl, triphenylenyl, penalenyl, pyrenyl, tetrasenyl, pentanesyl, Fluorenyl, indenyl, acenaphthylenyl, fluorenyl, benzofluorenyl, spirobifluorenyl, and the like, and condensed rings thereof, but are not limited thereto.
  • the spiro group includes a spiro structure, and may have 15 to 60 carbon atoms.
  • the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro bonded to a fluorene group.
  • the spiro group includes a group of the following structural formula.
  • the heteroaryl includes S, O, Se, N or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which heteroaryl is directly connected or condensed with another ring group.
  • the other ring group may be heteroaryl, but may also be other types of ring groups such as cycloalkyl, heterocycloalkyl, aryl, and the like.
  • the heteroaryl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 3 to 25 carbon atoms, 3 to 20 carbon atoms, and 3 to 10 carbon atoms.
  • heteroaryl examples include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, fura Zanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, oxdiazolyl, thiazinyl, dioxyyl, triazinyl, tetrazinyl, cy Nolinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, isoquinazolinyl, naphthyridyl, acridinyl, phenanthridinyl,
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 5.
  • R 1 to R 3 are the same as defined in the formula (1).
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 5-1.
  • R 4 is the same as defined in R 1 of Formula 1,
  • d is an integer of 0 to 4, and when d is 2 or more, a plurality of R 4 are the same as or different from each other,
  • R 1 to R 3 are the same as defined in the formula (1).
  • R 1 is-(L) m- (Z) n
  • L is substituted or unsubstituted C 6 to C 60 arylene; Or substituted or unsubstituted C 2 to C 60 heteroarylene,
  • n is an integer from 0 to 5
  • n is an integer of 1 to 3
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; substituted or unsubstituted C 1 to C 60 alkyl; substituted or unsubstituted C 3 to C 60 cycloalkyl; substituted Or unsubstituted C 6 to C 60 aryl, and substituted or unsubstituted C 2 to C 60 heteroaryl.
  • n is 0, or an integer of 1, 2, 3, 4 or 5, and when m is an integer of 2 or more, L is the same or different from each other.
  • n is an integer of 1, 2 or 3, and when n is an integer of 2 or more, Z is the same as or different from each other.
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; substituted or unsubstituted C 1 to C 60 alkyl; substituted or unsubstituted C 3 to C 60 cycloalkyl; substituted or Unsubstituted C 6 to C 60 aryl, and substituted or unsubstituted C 2 to C 60 heteroaryl.
  • L is substituted or unsubstituted C 6 Through C 20 Arylene; Or substituted or unsubstituted C 2 to C 20 N-containing heteroarylene.
  • L is C 6 to C 20 arylene; Or C 2 to C 20 N-containing heteroarylene, which may be further substituted with halogen.
  • L is phenylene; Naphthylene; Anthracenylene; Pyridylene; Pyrimidylene; Triazinylene; Fluorenylene; And carbazolylene, and may be further substituted with halogen.
  • Z is a substituted or unsubstituted C 6 Through C 60 Monocyclic or polycyclic aryl.
  • Z is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted pyrenyl , Substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, or substituted or unsubstituted spirobifluorenyl.
  • Z is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted pyrenyl , Substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, or substituted or unsubstituted spirobifluorenyl, and "Substituted or unsubstituted" is selected from halogen, C 1 to C 60 alkyl, substituted or unsubstituted C 3 to C 60 cycloalkyl, C 6 to C 60 aryl, C 2 to C 60 heteroaryl It means that it is substituted or unsubstituted
  • Z is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted pyrenyl , Substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, or substituted or unsubstituted spirobifluorenyl, and "Substituted or unsubstituted" is substituted or unsubstituted with at least one selected from halogen, methyl, cyclohexyl, phenyl, biphenyl, naphthyl, pyridyl and carbazolyl, or a substituent
  • Z is a substituted or unsubstituted C 2 Through C 60 Heteroaryl, wherein the heteroaryl is at least any one selected from N, O, S, Si and Se as a hetero atom It includes one.
  • Z is substituted or unsubstituted benzimidazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted naphthyridyl, substituted or unsubstituted Substituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted cynolinyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted oxdiazolyl , Substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzosilolyl, substituted or unsubstituted pyridyl, substituted
  • Z is substituted or unsubstituted benzimidazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted naphthyridyl, substituted or unsubstituted Substituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted cynolinyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted oxdiazolyl , Substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzosilolyl, substituted or unsubstituted pyridyl, substituted
  • Z is substituted or unsubstituted benzimidazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted naphthyridyl, substituted or unsubstituted Substituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted cynolinyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted oxdiazolyl , Substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzosilolyl, substituted or unsubstituted pyridyl, substituted
  • Z is X 1 and X 2 are the same as or different from each other, and each independently a substituted or unsubstituted C 6 to C 60 aromatic hydrocarbon ring; Or a substituted or unsubstituted C 2 to C 60 aromatic hetero ring.
  • the Is represented by any of the following structures.
  • Z One To Z 3 are the same as or different from each other, each independently S or O,
  • Z 4 to Z 9 are the same as or different from each other, and are each independently CY'Y ", NY ', S or O,
  • Y 'and Y are the same as or different from each other, and are each independently hydrogen; deuterium; substituted or unsubstituted C 1 to C 60 alkyl; or substituted or unsubstituted C 6 to C 60 aryl.
  • the Y 'and Y are the same or different from each other, and each independently hydrogen, deuterium, methyl, phenyl or naphthyl.
  • Z is -SiRR'R ", R, R 'and R" are the same as or different from each other, and each independently substituted or unsubstituted C 1 to C 60 alkyl ; Substituted or unsubstituted C 6 to C 60 aryl; And substituted or unsubstituted C 2 to C 60 heteroaryl.
  • Z is -SiRR'R ", R, R 'and R" are the same as or different from each other, and are C 6 to C 60 aryl.
  • Z is -SiRR'R ", R, R 'and R" is phenyl or biphenyl.
  • R, R 'and R are the same as or different from each other, and each independently substituted or unsubstituted C 1 to C 60 alkyl, substituted or unsubstituted C 6 to C 60 Aryl or substituted or unsubstituted C 2 to C 60 heteroaryl.
  • the R, R 'and R are the same or different from each other, and each independently methyl, ethyl, propyl, isopropyl, butyl, tertbutyl, phenyl, biphenyl, naphthyl, pyri Consisting of dill, pyrimidyl, anthracenyl, phenanthrenyl, chrysenyl, triphenylenyl, pyrenyl, fluorenyl, dimethylfluorenyl, carbazolyl, dibenzofuranyl, dibenzosilolyl and dibenzothiophenyl Selected from the group.
  • R 2 and R 3 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or C 6 -C 60 aryl.
  • R 2 and R 3 are the same as or different from each other, and each independently, hydrogen; Or deuterium.
  • R 2 to R 4 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Or C 6 -C 60 aryl.
  • R 2 to R 4 are the same as or different from each other, and each independently, hydrogen; Or deuterium.
  • Formula 1 may be selected from the following compounds.
  • the compounds described above may be prepared based on the preparation examples described below. In the following production examples, representative examples are described, but if necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, it is possible to change the starting materials, reactants, reaction conditions and the like.
  • the compound of Formula 1 may be prepared in the core structure as shown in the general formulas 1 and 2.
  • the compound of Formula 2 may be prepared in the core structure as shown in the general formula (1).
  • Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
  • Formula 1 is an illustration of an intermediate reaction for bonding a substituent to the position of R 1 in the core structure of Formula 2-1.
  • the last compound of Formula 1 is when R 1 in the formula 2-1 is phenyl substituted with Br.
  • the Br may be changed to another substituent if necessary, and the phenyl may be changed to another substituent by changing benzoyl chloride which is also a reactant.
  • the compound of Formula 2 may be prepared in the core structure as shown in the general formula (2).
  • Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
  • Formula 2 is an illustration of an intermediate reaction for bonding a substituent to the position of R 1 in the core structure of Formula 2-1.
  • the last compound of Formula 2 is the case where R 1 in the formula 2-1 is phenyl substituted with Br.
  • the Br may be changed to another substituent if necessary, and the phenyl may be changed to another substituent by changing benzoyl chloride which is also a reactant.
  • the organic light emitting device comprising the compound of Formula 1 described above.
  • the organic light emitting device according to the present application includes an anode, a cathode and at least one organic material layer provided between the anode and the cathode, one or more layers of the organic material layer comprises a compound of the formula (1).
  • FIG. 1 to 3 illustrate the stacking order of electrodes and organic material layers of organic light emitting diodes according to exemplary embodiments of the present application.
  • these drawings are not intended to limit the scope of the present application, the structure of the organic light emitting device known in the art can be applied to the present application.
  • an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is illustrated.
  • the present invention is not limited thereto, and as shown in FIG. 2, an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.
  • the organic light emitting diode according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306.
  • a hole injection layer 301 a hole transport layer 302
  • a light emitting layer 303 a hole transport layer 302
  • a hole blocking layer 304 a hole blocking layer 304
  • an electron transport layer 305 an electron injection layer 306.
  • the scope of the present application is not limited by such a lamination structure, and other layers except for the light emitting layer may be omitted, and other functional layers may be added as needed.
  • the organic light emitting device according to the present application may be manufactured by materials and methods known in the art, except for including the compound of Formula 1 in at least one layer of the organic material layer.
  • the compound of Formula 1 may constitute one or more layers of the organic material layer of the organic light emitting device alone. However, if necessary, the organic material layer may be mixed with other materials.
  • the compound of Formula 1 may be used as a hole injection material, a hole transport material, a light emitting material, a hole blocking material, an electron transport material, an electron injection material in the organic light emitting device.
  • the compound according to the exemplary embodiment of the present application may be used as a material of an electron injection layer, an electron transport layer, or a layer simultaneously performing electron injection and transport of an organic light emitting device.
  • the compound according to the exemplary embodiment of the present application may be used as the light emitting layer material of the organic light emitting device.
  • the compound may be used alone as a light emitting material, or may be used as a host material or a dopant material of the light emitting layer.
  • the compound according to the exemplary embodiment of the present application may be used as a phosphorescent host material of the organic light emitting device.
  • the compound according to the exemplary embodiment of the present application is included with the phosphorescent dopant.
  • the compound according to the exemplary embodiment of the present application may be used as a material of the hole blocking layer of the organic light emitting device.
  • anode material materials having a relatively large work function may be used, and a transparent conductive oxide, a metal, or a conductive polymer may be used.
  • the cathode material materials having a relatively low work function may be used, and a metal, a metal oxide, or a conductive polymer may be used.
  • hole injection material a well-known hole injection material may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or described in Advanced Material, 6, p.677 (1994).
  • Starburst-type amine derivatives such as TCTA, m-MTDATA, m-MTDAPB, polyaniline / dodecylbenzenesulfonic acid (polyaniline / dodecylbenzenesulfonic acid) or PEDOT / PSS (Poly (3, 4-ethylenedioxythiophene) / Poly (4-styrenesulfonate): poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate)), PANI / CSA (Polyaniline / Camphor sulfonic acid: polyaniline / camphorsulfonic acid) or PANI / PSS (Polyaniline / Poly (4-styrene-sulfonate): polyaniline / poly (4-styrenesulfonate)) and the like can be used.
  • Polyaniline / dodecylbenzenesulfonic acid polyaniline / dode
  • pyrazoline derivatives arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like may be used, and low molecular or polymer materials may be used.
  • Examples of the electron transport material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinomethane and derivatives thereof, and fluorenone Derivatives, diphenyl dicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like can be used, as well as high molecular weight materials as well as high molecular materials.
  • LiF is representatively used in the art, but the present application is not limited thereto.
  • a red, green or blue light emitting material may be used, and if necessary, two or more light emitting materials may be mixed.
  • a fluorescent material may be used as the light emitting material
  • a phosphorescent material may be used.
  • the light emitting material a material which combines holes and electrons injected from the anode and the cathode, respectively, to emit light may be used, but materials in which the host material and the dopant material are involved in light emission may be used.
  • the compound according to the present application is used as a phosphorescent host material
  • those known in the art may be used as the phosphorescent dopant material to be used together.
  • phosphorescent dopant materials represented by LL'MX, LL'L “M, LMXX ', L 2 MX and L 3 M can be used, but the scope of the present application is not limited to these examples.
  • L, L ', L ", X and X' are bidentate ligands different from each other, and M is a metal which forms an 8-sided complex.
  • M may be iridium, platinum, osmium or the like.
  • L is sp 2 It is an anionic bidentate ligand coordinated to M by carbon and hetero atoms, and X can function to trap electrons or holes.
  • Non-limiting examples of L include 2- (1-naphthyl) benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, thienylpyridin, phenylpyridine, benzothier Nylpyridines, 3-methoxy-2-phenylpyridine, thienylpyridines, tolylpyridine and the like.
  • Non-limiting examples of X include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.
  • Triethylamine (25 ml, 181.08 mmol) was added to a mixture of Compound 2-2 (24.6 g, 60.36 mmol) and THF (400 ml) in a round neck bottom flask under nitrogen, followed by stirring for 10 minutes.
  • a THF (35 ml) mixture of 2-naphthyl chloride (17.25 g, 90.54 mmol) was added at 0 ° C. and stirred for 3 h.
  • the organic layer was dried over MgSO 4 .
  • Triethylamine (26 ml, 191.4 mmol) was added to a mixture of Compound 2-2 (26 g, 63.8 mmol) and THF (450 ml) in a round neck bottom flask under nitrogen, followed by stirring for 10 minutes.
  • compound 18-2 (8 g, 13.97 mmol), (4- (1-phenyl-1 H-benzo [d] imidazol-2-yl) phenyl) boronic acid (( 4- (1-phenyl-1H-benzo [d] imidazol-2-yl) phenyl) boronic acid) (4.38g, 13.97 mmol), K 2 CO 3 (3.86g, 27.34 mmol), Pd (PPh 3 ) 4 (1.6g, 1.39 mmol) of 1,4-dioxane (1,4-Dioxane) / H 2 O (150ml / 30ml) mixed solution for 5 hours It was stirred at reflux.
  • Triethylamine (26 ml, 191.4 mmol) was added to a mixture of Compound 2-2 (26 g, 63.8 mmol) and THF (450 ml) in a round neck bottom flask under nitrogen, followed by stirring for 10 minutes.
  • THF 40 ml
  • 3-bromobenzoyl chloride 21 g, 95.7 mmol
  • the organic layer was dried over MgSO 4 .
  • Trifluoroacetic acid (46.5mL, 0.6mol) was added to a mixture of solid (68.9g, 0.25mol) and acetic acid (700ml) in a round neck bottom flask, and stirred at 100 ° C for 12 hours. . The solution cooled to room temperature was washed with acetic acid and hexane and filtered to obtain an ivory solid B-1. (27.3g, 42%)
  • Triethylamine (26 ml, 191.4 mmol) was added to a mixture of Compound 187-2 (26 g, 63.8 mmol) and THF (450 ml) in a round neck bottom flask under nitrogen, followed by stirring for 10 minutes.
  • Triethyl amine (45.6 ml, 328.98 mmol) was added to a mixture of Compound 237-2 (44.69 g, 109.66 mmol) and THF (500 ml) in a One neck rbf under nitrogen, followed by stirring for 10 minutes.
  • a target compound 275 was obtained by the same method as the preparation of compound 267 in Preparation Example 25, except that compound 3-bromobenzoyl chloride was used instead of 4-bromobenzoyl chloride. (9.0g, 69%)
  • a target compound 276 was obtained by the same method as the preparation of compound 268 in Preparation Example 26, except that compound 3-bromobenzoyl chloride was used instead of 4-bromobenzoyl chloride. (9.4g, 77%)
  • target compound 298 was obtained by the same method as the preparation of compound 101 in Preparation Example 11. (7.3g, 68%)
  • a target compound 304 was obtained by the same method as the preparation of compound 18 in Preparation Example 2, except that compound 237-4A was used instead of 18-2. (7.6g, 62%)
  • a target compound 292 was obtained by the same method as the preparation of compound 304 in Preparation Example 36, except that compound 4-bromobenzoyl chloride was used instead of 3-bromobenzoyl chloride. (5.9g, 48%)
  • a target compound 307-1 was obtained by the same method as the preparation of compound 237-3 in Preparation Example 17, except that compound 4-bromobenzoyl chloride was used instead of 3-bromobenzoyl chloride. (48.3g, 74%)
  • a target compound 307-2B was obtained by the same method as the preparation of compound 237-4 (B) in Production Example 17, except that compound 307-1 was used instead of 237-3. (18g, 36%)
  • a target compound 305 was obtained by the same method as the preparation of compound 296 in Preparation Example 34, except that Compound 307-2B was used instead of 237-4A. (8.9g, 73%)
  • a target compound 316 was obtained by the same method as the preparation of compound 298 in Preparation Example 35, except that Compound 307-4B was used instead of 237-4A. (7.8g, 67%)
  • a target compound 322 was obtained by the same method as the preparation of compound 18 in Preparation Example 2, except that compound 307-4B was used instead of 18-2. (6.8g, 59%)
  • a target compound 323-2 was obtained by the same method as the preparation of compound 77-2 in Preparation Example 9, except that compound 3,5-dibromobenzoyl chloride was used instead of 3-bromobenzoyl chloride. (43g, 88%)
  • a target compound 335 was obtained by the same method as the preparation of compound 323 in Preparation Example 43, except that compound 187-2 was used instead of 2-2. (8.9g, 70%)
  • a target compound 338 was obtained by the same method as the preparation of compound 326 in Preparation Example 44, except that compound 187-2 was used instead of 2-2. (9.2g, 83%)
  • a target compound 345 was obtained by the same method as the preparation of compound 333 in Preparation Example 45, except that compound 187-2 was used instead of 2-2. (9.1g, 74%)
  • a target compound 347 was obtained by the same method as the preparation of compound 323 in Preparation Example 43, except that compound 237-2 was used instead of 2-2. (8.9g, 74%)
  • a target compound 350 was obtained by the same method as the preparation of compound 326 in Preparation Example 44, except that compound 237-2 was used instead of 2-2. (9.8g, 88%)
  • a target compound 362 was obtained by the same method as the preparation of compound 326 in Preparation Example 44, except that compound 237-2 was used instead of 2-2. (98g, 89%)
  • a target compound 370 was obtained by the same method as the preparation of compound 333 in Preparation Example 45, except that 4-chloro-6-phenyl-1,3,5-triazine was used. (10.3 g, 84%)
  • a target compound 261 was obtained by the same method as the preparation of compound 76 in Preparation Example 8, except that compound 9-bromo-10-phenylanthracene was used instead of 2- (4-bromophenyl) benzo [d] thiazole. (5.3g, 74%)
  • a target compound 383 was obtained by the same method as the preparation of compound 237 in Preparation Example 17, except that compound 3-bromo-1,1'-biphenyl was used instead of 2-bromo-4,6-diphenylpyrimidine. (6.6g, 87%)
  • the target compound 393 was prepared by the same method as the preparation of compound 237 of Preparation Example 17. Got it. (7.2g, 71%)
  • Tables 1 and 2 show measured values of 1 H NMR (CDCl 3 , 200 MHz), and Table 2 shows measured values of field desorption mass spectrometry (FD-MS).
  • Figures 4 to 17 shows the PL or LTPL measurement graph of the compound.
  • the PL measurement was performed using a model name LS55 spectrometer from Perkin Elmer, the LTPL measurement was performed using a model name F7000 spectrometer from HITACHI, and analyzed on -196 ° C (77K) using liquid nitrogen.
  • FIG. 4 shows a PL measurement graph at 265 nm wavelength of Compound 37.
  • FIG. 6 shows a PL measurement graph at 298 nm wavelength of Compound 43.
  • FIG. 7 shows a LTPL measurement graph at 308 nm wavelength of Compound 43.
  • FIG. 8 shows a PL measurement graph at 278 nm wavelength of compound 44.
  • FIG. 9 shows a graph of LTPL measurements at 307 nm wavelength of compound 44.
  • FIG. 10 shows a PL measurement graph at 309 nm wavelength of Compound 76.
  • FIG. 11 shows a graph of LTPL measurements at 327 nm wavelength of compound 76.
  • FIG. 12 shows a PL measurement graph at 271 nm wavelength of Compound 98.
  • FIG. 13 shows a graph of LTPL measurements at 271 nm wavelength of compound 98.
  • FIG. 14 shows a PL measurement graph of 262 nm wavelength of Compound 248.
  • FIG. 15 shows a graph of LTPL measurements at 307 nm wavelength of compound 248.
  • FIG. 16 shows a PL measurement graph at 280 nm wavelength of Compound 267.
  • FIG. 17 shows a PL measurement graph of 325 nm wavelength of Compound 275.
  • the y axis is intensity and the x axis is wavelength (unit: nm).
  • the transparent electrode ITO thin film obtained from the glass for OLED was subjected to ultrasonic cleaning for 5 minutes using trichloroethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol and used.
  • the ITO substrate was installed in a vacuum deposition apparatus. Then, in a vacuum chamber, 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenyl amine (4,4', 4" -tris () on the ITO.
  • N, N- (2-naphthyl) -phenylamino) triphenyl amine: 2-TNATA) was vacuum deposited to a thickness of 600 mm 3 to form a hole injection layer.
  • N, N'-bis ( ⁇ -naphthyl) -N, N'-diphenyl-4,4'-diamine N, N'-bis ( ⁇ -naphthyl) -N was formed on the hole injection layer.
  • NPB N'-diphenyl-4,4'-diamine
  • a 200 ⁇ thick light emitting layer was vacuum deposited on the hole transport layer using a blue light emitting host material H1 and a blue light emitting dopant material D1 in a 95: 5 ratio.
  • lithium fluoride LiF was deposited on the electron transport layer as an electron injection layer with a thickness of 10 kW, and an anode was formed on the electron injection layer with an Al thickness of 1000 kW to form an OLED device.
  • An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1, except that the compound of Table 3 was used instead of E1 used in the electron transport layer in Comparative Example 1.
  • the organic light emitting display device using the compound of the present application as the electron transport layer material has a lower driving voltage, improved luminous efficiency and a markedly improved lifetime as compared with Comparative Example 1.

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WO2020101316A1 (ko) * 2018-11-12 2020-05-22 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2020101314A1 (ko) * 2018-11-12 2020-05-22 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
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WO2020101314A1 (ko) * 2018-11-12 2020-05-22 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
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